CA1042923A - Bromostyrene, dibromostyrene et bromures d'alkyle - Google Patents

Bromostyrene, dibromostyrene et bromures d'alkyle

Info

Publication number: CA1042923A
Authority: CA; Canada
Prior art keywords: bromoethyl; bromostyrene; bromobenzene; products; bromo
Prior art date: 1973-08-04
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA290,898A

Other languages

English (en)

Inventor

Ella Cohen

Stephen Daren

Moshe Levy

David Vofsi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Yeda Research and Development Co Ltd

Original Assignee

Yeda Research and Development Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-08-04

Filing date

1977-11-15

Publication date

1978-11-21

1977-11-15 Application filed by Yeda Research and Development Co Ltd filed Critical Yeda Research and Development Co Ltd

1978-11-21 Application granted granted Critical

1978-11-21 Publication of CA1042923A publication Critical patent/CA1042923A/fr

Status Expired legal-status Critical Current

Links

YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 title claims abstract description 13
238000004519 manufacturing process Methods 0.000 title claims abstract description 7
150000001347 alkyl bromides Chemical class 0.000 title claims abstract description 4
CYLVUSZHVURAOY-UHFFFAOYSA-N 2,2-dibromoethenylbenzene Chemical compound BrC(Br)=CC1=CC=CC=C1 CYLVUSZHVURAOY-UHFFFAOYSA-N 0.000 title description 3
238000000034 method Methods 0.000 claims abstract description 21
239000003054 catalyst Substances 0.000 claims abstract description 14
RUGOFYNHMCFJFD-UHFFFAOYSA-N 1-bromo-2-(2-bromoethyl)benzene Chemical compound BrCCC1=CC=CC=C1Br RUGOFYNHMCFJFD-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 3
150000001340 alkali metals Chemical class 0.000 claims abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 14
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
229940102396 methyl bromide Drugs 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 4
QARVLSVVCXYDNA-UHFFFAOYSA-N phenyl bromide Natural products BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 4
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims description 2
239000000376 reactant Substances 0.000 claims description 2
239000012159 carrier gas Substances 0.000 claims 1
239000007789 gas Substances 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
239000000047 product Substances 0.000 description 13
239000000203 mixture Substances 0.000 description 8
239000000758 substrate Substances 0.000 description 8
239000003085 diluting agent Substances 0.000 description 7
239000000178 monomer Substances 0.000 description 6
229910000039 hydrogen halide Inorganic materials 0.000 description 5
239000012433 hydrogen halide Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000006227 byproduct Substances 0.000 description 4
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 3
-1 bromophenyl ethyl Chemical group 0.000 description 3
238000006704 dehydrohalogenation reaction Methods 0.000 description 3
230000008021 deposition Effects 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
239000000463 material Substances 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000007269 dehydrobromination reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
238000004508 fractional distillation Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000012263 liquid product Substances 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
238000000197 pyrolysis Methods 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
VHFRWIVIJXEZDB-UHFFFAOYSA-N 1,2-dibromo-3-(2-bromoethyl)benzene Chemical compound BrCCC1=CC=CC(Br)=C1Br VHFRWIVIJXEZDB-UHFFFAOYSA-N 0.000 description 1
DGSQMAWMWINPRH-UHFFFAOYSA-N 1-bromo-1-phenylethanol Chemical compound CC(O)(Br)C1=CC=CC=C1 DGSQMAWMWINPRH-UHFFFAOYSA-N 0.000 description 1
HVRUGFJYCAFAAN-UHFFFAOYSA-N 1-bromo-2-ethylbenzene Chemical class CCC1=CC=CC=C1Br HVRUGFJYCAFAAN-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
101100381997 Danio rerio tbc1d32 gene Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
101100381999 Mus musculus Tbc1d32 gene Proteins 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
238000010276 construction Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
239000002316 fumigant Substances 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
150000005171 halobenzenes Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
229910001510 metal chloride Inorganic materials 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000011269 tar Substances 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229920006305 unsaturated polyester Polymers 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
125000002348 vinylic group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA290,898A 1973-08-04 1977-11-15 Bromostyrene, dibromostyrene et bromures d'alkyle Expired CA1042923A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2339612A DE2339612C2 (de)	1973-08-04	1973-08-04	Verfahren zur gleichzeitigen Herstellung von Bromstyrol oder Dibromstyrol und einem Alkylbromid
CA179,044A CA1032183A (fr)	1973-08-04	1973-08-17	Production de bromostyrene, de dibromostyrene et de bromures alkyles

Publications (1)

Publication Number	Publication Date
CA1042923A true CA1042923A (fr)	1978-11-21

Family

ID=25667329

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA179,044A Expired CA1032183A (fr)	1973-08-04	1973-08-17	Production de bromostyrene, de dibromostyrene et de bromures alkyles
CA290,898A Expired CA1042923A (fr)	1973-08-04	1977-11-15	Bromostyrene, dibromostyrene et bromures d'alkyle

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CA179,044A Expired CA1032183A (fr)	1973-08-04	1973-08-17	Production de bromostyrene, de dibromostyrene et de bromures alkyles

Country Status (2)

Country	Link
CA (2)	CA1032183A (fr)
DE (1)	DE2339612C2 (fr)

1973
- 1973-08-04 DE DE2339612A patent/DE2339612C2/de not_active Expired
- 1973-08-17 CA CA179,044A patent/CA1032183A/fr not_active Expired
1977
- 1977-11-15 CA CA290,898A patent/CA1042923A/fr not_active Expired

Also Published As

Publication number	Publication date
CA1032183A (fr)	1978-05-30
DE2339612C2 (de)	1982-05-19
DE2339612A1 (de)	1975-02-20

Publication	Publication Date	Title
JPH0427218B2 (fr)	1992-05-11
Ichikawa et al.	1992	A facile synthesis of disubstituted 1, 1-difluoro-1-alkenes via double transmetalation of 2, 2-difluorovinylboranes
EP0004636B1 (fr)	1982-07-07	Procédé de préparation de benzotrifluoride et ses dérivés
EP0168803B1 (fr)	1990-09-26	Procédé de production de p-isobutylstyrène
US3980722A (en)	1976-09-14	Production of bromostyrene, dibromostyrene and alkyl bromides
US3737469A (en)	1973-06-05	Process for the production of bromostyrene and alkyl bromide
US2481157A (en)	1949-09-06	Treatment of halo-hydrocarbons
US3966831A (en)	1976-06-29	Production of bromostyrenes
US4163753A (en)	1979-08-07	Process for the simultaneous preparation of aromatic acid chlorides and aliphatic acid chlorides
US3836592A (en)	1974-09-17	Isomerization of 1,2-dichloro-3-butene to 1,4-dichloro-2-butene
US2481160A (en)	1949-09-06	Production of halocycloalkanes
US2501597A (en)	1950-03-21	Production of organic halogen compound
US4038331A (en)	1977-07-26	Catalytic process for preparation of perfluoroalkyl substituted aromatic compounds
US4393246A (en)	1983-07-12	Process for brominating side chain of m-phenoxytoluene
US2981755A (en)	1961-04-25	Unsaturated halogenated cyclopentene compounds
US3689580A (en)	1972-09-05	Preparation of halodienes
US2626962A (en)	1953-01-27	Production of haloolefinic compounds
US4341899A (en)	1982-07-27	Vapor phase dechlorination process
US3312747A (en)	1967-04-04	Production of 4-halobutene-1
JPS6043051B2 (ja)	1985-09-26	ｍ−フェノキシトルエンの側鎖の臭素化方法
US2482208A (en)	1949-09-20	Process for making styrene and its derivatives
JP3953098B2 (ja)	2007-08-01	モノマー前駆体異性化
EP0646560A1 (fr)	1995-04-05	Procédé de préparation d'un hydrocarbure fluoré
US4960962A (en)	1990-10-02	Selective dehydrobromination
US5451703A (en)	1995-09-19	Process for the preparation of biaryls